


Now or Never

by reapingwithjoy



Series: Now or Never [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - High School, Dean Plays Guitar, Drive-In, Fluff, High School, M/M, Summer
Language: English
Status: In-Progress
Published: 2013-05-04
Updated: 2013-05-04
Packaged: 2017-12-10 08:25:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,812
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/783935
Author URL: https://archiveofourown.org/users/reapingwithjoy/pseuds/reapingwithjoy
Summary: <blockquote class="userstuff">
              <p>The summer before he goes off to college, Dean meets Castiel at their local drive-in and decides he has to get to know the boy.</p>
            </blockquote>





	1. Spent My Evenings Down at the Drive-In

**Author's Note:**

> Based around my favorite rock song, Summer of 69' by Bryan Adams. Sadly, the time period is not in 1969 'cause I know nothing of the drive-ins in 1969 and it has nothing to do with the sexual act. I hope you enjoy it as much as I do!

Drive-Ins were part of the Winchester summer tradition. John would save some money at the end of the week and take the boys to see whichever high end, summer blockbuster came out that week. It had a more wholesome feeling than the movie theaters; well, it seemed that way to them.

"Hey, Dean, why don't you go over to the concession stand and get us some popcorn," his dad asked, handing him a ten dollar bill.

"Yeah, sure."

It was the summer before Dean went off to college and he wanted to revel in his family's crazy traditions before he set off alone.

Walking to the concession stand near the back of the field, Dean was blinded by the headlights of cars coming in to see the show. Making sure he didn't get hit, he made it to the dusty stand, taking his place in line behind an average height guy with shaggy brown hair who was talking aimlessly to a slightly taller boy with tousled, I-don't-give-a-fuck dark brown hair and amazingly blue eyes; both about his age. Dean couldn't help but stare at the blue-eyed boy who was leaning against the wooden railing, obviously bored with whatever his friend was saying. He looked too serious to be his age, probably one of those 'old souls' people always talked about. Nonetheless, Dean was intrigued, and the flip-flopping in his stomach alerted him that he definitely felt something.

The shorter boy moved up to the counter, ordering numerous candies and giving Dean the opportunity to talk to his mystery man.

"Is he planning on sharing with the entire audience?" Dean teased with a smile.

Blue Eyes smirked in response, answering with a rough, deep voice, "No, probably not. My brother here has a larger appetite for sweets than most children."

Dean laughed briefly. "I don't blame him. I love me some suckers," he tossed back, a wicked smile spreading across his face.

Either Dean was losing his touch, or the boy missed his attempt at flirting because he answered with a glare at his brother. "As does he."

Dean waited a beat to see if he would say anything more before sticking out his hand to offer an introduction, "Dean. Dean Winchester."

Returning his gaze to Dean, the boy raised his hand, clasping the extended hand, "Castiel Novak."

"Hmmm... Castiel," he repeated, letting the strange, but somehow fitting name roll off his lips and warm his entire body, "I like it. It’s interesting."

Castiel's brother had already wandered off with arms full of candy, leaving the two guys to order. "Thanks. My parents like obscure, religious names."

The lady behind the counter brought back Castiel's hot dog and Dean's large popcorn with extra butter. They paid and walked to the entrance of the concession stand. The drive-in was usually packed Friday nights and today was no exception; forty plus cars were scattered across the field, facing their respective screens. The movies were about to start, but Dean didn't want to leave Castiel, not yet.

"So which movie are ya watching," Dean asked, glancing over at Castiel before a light blush creeped over his face at the sight of him taking a bite of his hot dog. He took his time to chew and swallow before replying, his throat distracting Dean. "I am watching The Raven with my brothers. And yourself?"

"The Avengers. My little brother has been nerding out about it since they announced it was coming out, but I'm excited to see it, too. Nothing wrong with a good superhero movie, ya know?"

Castiel smiled slightly and nodded, "Yes, I agree with you. Perhaps next week we shall watch that."

The two were silent for a bit before they noticed the trailer for a movie coming out soon starting to play on the screens across the way.

"Well, I believe I should be going now," Castiel began to walk away. Dean had to do something quick if he wanted to make sure he was going to see those blue eyes again. "It was nice to-"

"Uh, Castiel," Dean stepped towards him so they were but a hands length away, "We should..." He laughed nervously, looking down at his shoes before looking up again, "We should trade phone numbers. You know. Tell me how you like The Raven."

A rosy tint accompanied Castiel's small smile, the warm light coming from the concession stand making him look ethereal. "Yes, I'd like that, Dean."

Dean felt as if the butterflies in his stomach were having a wrestling match, but that didn't stop the brilliant grin that spread across his face. He pulled his cell phone out of his pocket, passing it to Castiel, the other doing the same for him. Never had it felt more satisfying to put his number into someone's phone. They returned their phones to each other and began to walk in the direction of their cars, a nice silence between them. Dean didn't know how he could feel that comfortable with someone he just met, but he didn't question it. He couldn't remember the last time the violent butterflies in his stomach had stirred like this, so he might as well enjoy it.

They paused once more before parting ways, shaking hands a little bit longer than was necessary. "I'll see you around Castiel."

The other boy nodded once. "Alright, Dean."

It wasn't a 'no' so that was good enough for Dean. Releasing the warmth of Castiel's hand, Dean turned around and walked to his dad's car, popcorn in his arms and a smile on his face. 

“What took you so long? Dean… you okay?” Sam asked upon seeming the strange grin on his brother’s face.

He handed Sam the popcorn and took his seat on one of the chairs that they keep in the car for moments like these. “Yeah. Just made a new friend,” he responded with small smile. 

Sam took the seat next to him, popping some popcorn in his mouth as the movie began to play, the sound coming from their portable radio set to the correct station. “A friend or a _friend_?” Putting emphasis on the last word with an elbow nudge. 

“Shut up.”

“Both of you hush up,” their dad exclaimed, keeping his focus on the movie. Both of the boys turn their attention to the screen before them. 

Dean smiled; the weight of the phone in his pocket reminding him of the strange boy with the blue eyes. He took out his phone to scan though his contact list, stopping at Castiel’s name, wondering if it would be too soon to text him. It had only been twenty minutes. _Yeah, no, too soon._ He put his phone on standby and let it sit on his lap. 

Thirty more minutes passed with Dean picking up his phone and putting it back on his lap at least ten more times. By the eleventh time, Dean was about to give up, when his phone vibrated.

Castiel Novak: This movie is not what I expected it to be.

Dean bit his lip and smiled once more, the stupid butterflies acting up again. He had it, bad. 

Dean: That sux man. Avengers is kick ass.

“Is that her? Or him?” Sam craned his neck to look at his phone, “How do you get their numbers so fast, Dean?” 

Dean shoved his face away as another text arrived, “Watch the movie, Snoopy. It’s none of your business.” 

Castiel Novak: Yes, it does look entertaining.

He turned his head around to see if he could catch a glimpse of Castiel, but all he could see was a sea of cars.

Dean: Watchin the wrong screen cas? Ur gonna spoil it!

Castiel Novak: Cas?

_Shit, where did that come from?_

Dean: Sry idk where that came from.

Before the nerves could settle in, Castiel responded. 

Castiel Novak: It’s alright Dean. I like it. It was just unexpected.

He released the breath he didn’t know he had been holding. “Dean, stop texting your friend and watch the movie,” his father admonished him. 

“Sorry, Dad.”

Dean: :) sry g2g Txt u after movies done.

Dean spent the rest of the movie wondering what to say to get a chance with Castiel _(No, Cas)_. Needless to say, Dean doesn’t know how the movie ended.


	2. Standin' on Your Momma's Porch

**Summary for the Chapter:**

> Castiel and Dean go on their first date.

Dean was smitten, everyone could see it plain as day. His mom and dad heard him humming pleasantly while doing dishes and he didn't complain when he was asked to mow the lawn, which was a miracle. All this started after he began receiving more text that Friday night.

"I believe our boy has found someone, John," Mary whispered to her husband after watching Dean walk past the living room with his phone in hand and a goofy smile on his face.

"Guess I'm losing my car," he joked, earning him a playful smack on the arm.  
\------------  
A flashing light flickered onto the phone on his pillow.

Cas: What are you up to?

Dean paused his guitar playing to answer the text. He had changed the name on his phone, proud to display his personal nickname for the guy that has been consuming his thoughts for the past four days.

Dean: Playin guitar. Wbu?

Cas: I am watching the bees. You play the guitar?

In the little time he had known him, Dean had learned that Cas went to the local private school, explaining why he never met him. He lived with his grandparents and his two older brothers, Gabriel, who was the guy with the sweet tooth, and Balthazar, who was also at the drive-in that night. Castiel has a cat named Bast and a garden, both of which Cas holds dear to him. He also learned that he loved to hear Cas' voice, and he especially loved making him laugh; a husky little laugh that made Dean warm with happiness.

Dean: Can I call u?

Cas: I don't know. Can you?

Dean huffed and rolled his eyes with a fond smile. Grammar nazi. He searched for recent contacts, pressing the first name on the list.

Dean bit his lip anxiously. He'd been waiting for the right time to ask Cas out for that Friday, not wanting to ask prematurely for fear of getting rejected. This still may be too early, but summer is only so long.

Castiel picked up after the third ring, greeting him with a kind, "Hello Dean."

"Yes."

"What?" Castiel asked with a confused tone.

"Yes. I do play the guitar."

Cas hummed in understanding. "Are you any good?"

Dean put his guitar on it's stand then layed on his back. "Well, Sammy says I'm good, but I just bought this guitar at the end of the school year. I ain't no Jimmy Page."

"Who is Jimmy Page," he asked a little too seriously to be joking.

"'Who is Jimmy Page?' Guitar legend! Led Zeppelin? Please tell me you know who they are!"

"No, I'm afraid I do not." Dean could practically see the frown that accompanied that statement.

"Well, it's a good thing you met me. I'll introduce you to the awesome that is classic rock."

"Sounds exciting," a soft smile playing on his lips.

"Oh, it is." A pause. "So um, Cas..."

"Yes?"

"Would you like to hang out on Friday? I could ask for the day off work, we could go to the state park. They just renovated it and my dad says it looks pretty good. Then after we could go to the drive-in... I mean, if that's okay with you. I know you usually go with your brothers and I-"

"Dean!" Cas interrupted his little nervous rant, "I would love that."

"Yeah? Okay, good." Dean released a breath, his lips curling into a grin.

"Good."

The two stayed quiet for a bit, just relaxed in their silence. A call for Cas on his end saying that dinner was ready ended their silent exchange, but Dean's elated smile didn't leave his face. He couldn't wait for Friday to arrive.  
\-----------  
"Dad, can I have the keys to the Impala?"

"Ha! See! What'd I tell you Mary?!" Dean's dad called out from the kitchen table to his mom folding clothes in the living room.

"What?" Dean asked, puzzled.

"Nothing. Does this have to do with the person you have been texting all week?"

"Yes, sir."

"Why don't you take your mom's car?"

"Cause yours is nicer! And anyways, you said I could have it when I go off to college so why not start a little early?"

"Alright... Will we get to meet this mystery person?"

Dean smiled a little. "Let's see how today goes first, Dad."

He got up from his seat, putting his bowl of cereal in the sink and taking the keys from the key bowl. At the door he called out, "Wish me luck!" which both of his parents offered him before he closed the door and left to go pick up Castiel.  
\-----------  
The modesty of Castiel's home surprised him. He figured that anyone who went to a private school would be living the high life. This was not the case for Cas.

The Novaks lived just outside of town in a two story farm house that was a pleasant yellow color with a wraparound porch, a small pond in the backyard, and the nearest neighbor lived a quarter of a mile away. It was picturesque.

When Dean arrived, Cas was sitting on the porch railing waiting for him. Upon seeing Dean, he hopped off the porch and walked towards the car.

Dean was beginning to feel awkward. Should he get out of the car to greet him or should he just wait there? If he does get out how does he greet him? These thoughts make him fidget in his seat, but before he could make a decision, Cas slid into the passenger's seat.

"Nice to see you again, Dean."

The look Cas was giving him, like he was both nervous and happy to be there made Dean relax a bit. Cas was feeling the same thing as he was.

"Hey, Cas."

The use of his nickname made Cas' eyes shine and a genuine smile spread across his face. This was the first time Dean saw the reaction in person and, boy, did he want to kiss him silly. Deciding against it, he turned the car around to go down the road that led back to the main road.  
Castiel sat rod straight with his hands neatly folded on his lap, like the nerves just ran straight through him. As if by instinct, Dean grabbed his elbow tenderly, making Castiel jump and then visibly relax. "You okay?" Dean asked, hushed and concerned.

Cas turned his face to him, a smile reaching his lips and a nod to answer. _This guy is seriously beautiful._ The thought made his lip quirk. He let go of his elbow and turn his attention back to the road, away from the warm blue eyes.

The rest of the fifteen minute drive was quiet besides the roar of the engine, exchanging a few glances at each other. Cas looked as if he belonged in Dean's front seat; now relaxed, he leaned back into his seat watching the scenery pass by, his tousled hair dancing with the wind, and the light of the sun framing his face so he, once again, looked nothing short of angelic. It took Dean all his might to keep his eyes on the road instead of tracing the profile of Cas' face with his eyes.

As they turned into the park entrance Dean began to feel nervous once more, self-doubt seeping in. Dean parked the car across from a trail that lead up a huge hill that overlooked the town called 'Layla's Peak.' "So, I was thinking we could walk up to 'The Peak," Dean suggested fiddling with the steering wheel as he looked from Castiel to the path ahead.

Cas watched him as he played with the steering wheel, making Dean stop and put his hands in his lap. "That sounds nice. I've never been. I’ve always heard it was a nice view though."

"Okay, let's go."

Both boys got out of the car; Dean double checking they locked the car or else he'd have his ass served to him. The two soon fell into step with each other walking along the packed dirt path. "You've really never gone up there?" Dean asked, inquiring on Cas' previous statement. It seemed strange to think that someone who lived in the area has never gone up to Layla's Peak; it was kind of a rite of passage to any of the kids in the area.

"No. I know it's kind of a big deal here, well my grandparents say so, but I never got the chance to... Well, until now," he added, looking over at Dean with a shy smile that warmed Dean's body. Cas turned his attention back to the trail that was starting to get steeper and a bit rockier.

"And why is that?"

"Well, My brothers and I moved in with my grandparents at the end of my eighth grade year." He paused as if he was deciding whether to continue. "My, um, my parents died that year."

Dean's heart sank. He couldn’t imagine losing one of his parents, but both? He could not possibly fathom what Cas' went though.

The two stood on the stone steps that were placed to help get up the hill, Castiel one step ahead. He looked up to Cas, not realizing they stopped.

"Cas, I'm so sorry," he said genuinely. This made Castiel smile fondly.

"It's alright Dean. I have come to terms with my loss."

Dean stared into Castiel's eyes, darker than usual with the shade from the trees, trying to understand this enigma in front of him. He has a feeling that no matter how long he spends with Castiel, he will never truly understand him. 

"You are really amazing," Dean says under his breath. 

"What was that?" Castiel shifted towards him, making the stone he was standing on shift, causing Cas to fall back, arms flailing for balance. Dean, thinking fast, caught him by his waist, but his weight made Dean fall on his ass with Cas falling perpendicularly onto his lap.

Both boys groaned simultaneously, which caused them to laugh. Castiel sat up on Dean's lap, reaching a hand out to pull Dean off his back. "Are you alright Dean?" He sat up and placed the hand not holding Cas' behind him to hold him up. Dean looked down at the pair's hands and intertwined them, then looking up to Cas' eyes with a grin. "Yeah, I'm good. You?"

"I'm fine, thanks to you." The smile on Castiel's face reached his eyes. "Sorry for making you fall."

"You can fall on me anytime," Dean said smoothly. Yeah, it was cheesy, but with Cas, he didn't really care.  
\-----------  
The remainder of the daylight was spent on top of the hill. They talked aimlessly of anything that popped in their minds; what they wanted to do in the future, funny stories from their past, and sometimes nothing at all.

The two lied on their backs, hands entwined, watching the clouds go by, never growing bored of each other’s company. They watched the sunset; watching the colors change from blue to purple to orange and yellow, the awe in Cas' face making Dean's heart race. _If I move in a bit closer, I could kiss him..._ Adrenaline pumped through Dean's veins. _Do it._

Just as he inched closer, Cas looked down at his watch. "Shoot! We're going to be late to the movie," Cas began to walk back down the hill, pulling Dean with him. Dean barely budged, startled by the sudden mood change.

"Dean?" Cas asked, looking puzzled by Dean's face.

He shook his head to get back into focus, "Sorry. You're right let's go." Dean gently squeezed Cas' hand to reassure him when Cas still looked worried. Dean guessed it worked because the look disappeared and both of them made their way back to the car, just barely making the movie's opening sequence.

"Don't spoil it for me," Cas warned him, wrapping his arms around Dean's lower torso.

"Trust me, I won't," Dean responded blushing, placing is right arm over Cas' shoulder. "I don't even know what happens," he murmured while trying to suppress a smile.

"What was that?"

"Nothing," his thumb stroking Cas' shoulder. "Nothing."

They sat like that for the rest of the movie, both of them nodding off a few times, only to be woken up by a poke or a caress by the other.  
\-----------  
"So..." Cas began as Dean walked him up to his front porch, "Is this how you hang out with all your friends," obviously teasing Dean.

Dean let out a huff of laughter, scratching the back of his neck and looking down at his shoes only to look back up at Castiel. "No, definitely not.” 

"Good," Cas taking his hand as he stood on the steps of his porch, "I wouldn't want to be jealous."

He smiled at that. They stood in silence for a bit, pleased smiles on their faces. Dean played with Cas's hands as he tried to engrain the memory into his brain. Him standing on the bottom step with Cas one step up. They were so close, if he just leaned up he could claim the kiss time stole from him.

_Now. Kiss him._

Dean leaned up to hover over Cas' lips, just for a second, closing his eyes to breathe in the moment; the warmth of the summer air intensified by their closeness, the feeling that he had a pit in his stomach that he was willingly about to jump into. He didn’t even think twice before jumping in.  
Despite the pause, their noses bumped slightly. They adjusted their heads, lips slotting into place; Cas' lips were so much smoother than they looked. The kiss was slow and patient, softly sucking at each other’s lips. They were caught up in each other; Dean running his hands up Cas' chest, letting them rest on both sides of his neck, feeling the speeding pulse there. Cas slid his hands up Dean's strong arms to let one hand hold Dean's bicep while the other stroked the nape of his neck. 

It was the gentlest first kiss Dean ever had, but it left him more breathless than any of the ones before.

Dean pulled back, resting his forehead on Cas' to take in a deep breath. He watched Cas bushed his nose against his, his breath ghosting his lips. "Dean," Cas breathed out.

"Cas?"

A soft smile passed Cas' lips, "I wish that this day could last forever."

Dean pulled him in close pecking his lips once, wanting nothing more than to have Cas sleep next to him that night. "Me too, Cas."


End file.
